Well, I usually use portraits that I find on the webs, mostly because in most cases I first find interesting picture, and then it inspires me to do certain characters. And most of PBP games I play
require players to have character image. At least once I saw player getting extra points because of how cool GM thought his picture is. I try to use only original-characters portraits, as in, not characters from games or movies or anime or whatever. Mostly because I want to think about my character while looking at the portrait, not about Sasuke\Beatrice\whatever.
One of my GMs will look badly at you for playing with picture of non-original character. Also, some people in my circles tend to HATE anime pictures and won't allow them, and only heroes with real photos are allowed. Which makes games looks like hollywood movie ;P.
One of my friends spends a lot of time drawing her characters by hand, and well, everytime I have occasion of playing with her, I trick her into drawing the wole team, which results in cute pics.
Of people I know, only my gf dislikes using pictures, as it shackles imagination, which I think may have some truth in it. I remember that describing one of my characters from zero, without any picture to look at was super fun and helped flesh her out, giving me ideas. So I may try it, also because It will help improve my descriptions.
